Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 19, 2005, Pages 5600-5612

  Cichewicz, Robert H ^a   Clifford, Laura J ^a   Lassen, Peter R ^b,c   Cao, Xiaolin ^b   Freedman, Teresa B ^b   Nafie, Laurence A ^b   Deschamps, Joshua D ^a   Kenyon, Victor A ^a   Flanary, Jocelyn R ^a   Holman, Theodore R ^a   Crews, Phillip ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SYRACUSE UNIVERSITY   (United States)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Atropisomer; Curcuphenol; Dicurcuphenol; Didiscus aceratus; Dimer; Laccase; Lipoxygenase; Vibrational circular dichroism (VCD)

Indexed keywords

DICURCUPHENOL A; DICURCUPHENOL B; DICURCUPHENOL C; DICURCUPHENOL D; DICURCUPHENOL E; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CIRCULAR DICHROISM; CYTOTOXICITY; DIMERIZATION; ENZYME INHIBITION; HYDROXYLATION; SPONGE (PORIFERA); STEREOCHEMISTRY; VIBRATION;

ANIMALS; ARACHIDONATE 12-LIPOXYGENASE; ARACHIDONATE 15-LIPOXYGENASE; CATALYSIS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LACCASE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PORIFERA; SESQUITERPENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

DIDISCUS ACERATUS;

EID: 23944445604     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.06.020     Document Type: Article

References (62)

1. N. Fusetani, H.J. Wolstenholme, K. Shinoda, N. Asai, S. Matsunaga, H. Onuki, and H. Hirota Tetrahedron Lett. 33 1992 6823
2. M.S. Butler, R.J. Capon, R. Nadeson, and A.A. Beveridge J. Nat. Prod. 54 1991 619
3. C.-J. Li, F.J. Schmitz, and M. Kelly J. Nat. Prod. 62 1999 1330
4. N.K. Gulavita, E.D. De Silva, M.R. Hagadone, P. Karuso, P.J. Scheuer, G.D. Van Duyne, and J. Clardy J. Org. Chem. 51 1986 5136
5. K.A. El Sayed, M. Yousaf, M.T. Hamann, M.A. Avery, M. Kelly, and P. Wipf J. Nat. Prod. 65 2002 1547
6. A.E. Wright, S.A. Pomponi, O.J. McConnell, S. Kohmoto, and P.J. McCarthy J. Nat. Prod. 50 1987 976
7. N. Fusetani, M. Sugano, S. Matsunaga, and K. Hashimoto Experientia 43 1987 1234
8. A.D. Rodríguez, and B. Vera J. Org. Chem. 66 2001 6364
9. B.W. Sullivan, D.J. Faulkner, K.T. Okamoto, M.H.M. Chen, and J. Clardy J. Org. Chem. 51 1986 5134
10. B. Harrison, and P. Crews J. Org. Chem. 62 1997 2646
11. J. Peng, S.G. Franzblau, F. Zhang, and M.T. Hamann Tetrahedron Lett. 43 2002 9699
12. I. Kitagawa, N. Yoshioka, C. Kamba, M. Yoshikawa, and Y. Hamamoto Chem. Pharm. Bull. 35 1987 928
13. H. Nakamura, J. Kobayashi, Y. Ohizumi, and Y. Hirata Tetrahedron Lett. 25 1984 5401
14. K.E. Kassulke, B.C.M. Potts, and D.J. Faulkner J. Org. Chem. 56 1991 3747
15. H.T. D'Armas, B.S. Mootoo, and W.F. Reynolds J. Nat. Prod. 63 2000 1593
16. A.J. Freyer, A.D. Patil, L. Killmer, G. Zuber, C. Myers, and R.K. Johnson J. Nat. Prod. 60 1997 309
17. S.L. Miller, W.F. Tinto, S. McLean, W.F. Reynolds, and M. Yu J. Nat. Prod. 58 1995 1116
18. F. McEnroe, and W. Fenical Tetrahedron 34 1978 1661
19. F.J. Schmitz, D.P. Michaud, and K.H. Hollenbeak J. Org. Chem. 45 1980 1525
20. G.M. König, and A.D. Wright J. Nat. Prod. 60 1997 967
21. T. Suzuki, H. Kikuchi, and E. Kurosawa Chem. Lett. 10 1980 1267
22. F. Valeriote, T. Corbett, P. LoRusso, R.E. Moore, P.J. Scheuer, G. Patterson, V. Paul, G. Grindely, R. Bonjouklian, H. Pearce, and M. Stuffness Int. J. Pharmacog. 33 Suppl. 1995 59
23. L.A. Nafie, and T.B. Freedman N. Berova K. Nakanishi R.W. Woody Circular Dichroism 2nd ed. 2000 Wiley-VCH New York 97 131
24. N. Berova K. Nakanishi R.W. Woody Circular Dichroism 2nd ed. 2000 Wiley-VCH New York
25. N. Berova, B. Borhan, J.G. Dong, J. Guo, X. Huang, E. Karnaukhova, A. Kawamura, J. Lou, S. Matile, K. Nakanishi, B. Rickman, J. Su, Q. Tan, and I. Zanze Pure Appl. Chem. 70 1998 377
26. T.W. Sam S.M. Colgate R.J. Molyneux Bioactive Natural Products: Detection Isolation and Structure Elucidation 1993 CRC Press Boca Raton 441 456
27. J.N.A. Hooper J.N.A. Hooper R.W.M. Van Soest JNA Systema Porifera: A Guide to the Classification of Sponges Vol. 1 2002 Kluwer Academic New York 755 772
28. F. Valeriote, C.K. Grieshaber, J. Media, H. Pietraszkewicz, J. Hoffmann, M. Pan, and S. McLaughlin J. Exp. Ther. Oncol. 2 2002 228
29. T. Amagata, S. Whitman, T.A. Johnson, C.C. Stessman, C.P. Loo, E. Lobkovsky, J. Clardy, P. Crews, and T.R. Holman J. Nat. Prod. 66 2003 230
30. J. Carroll, E.N. Jonsson, R. Ebel, M.S. Hartman, T.R. Holman, and P. Crews J. Org. Chem. 66 2001 6847
31. R.H. Cichewicz, V.A. Kenyon, S. Whitman, N.M. Morales, J.F. Arguello, T.R. Holman, and P. Crews J. Am. Chem. Soc. 126 2004 14910
32. E.N. Segraves, R.R. Shah, N.L. Segraves, T.A. Johnson, S. Whitman, J.K. Sui, V. Kenyon, R.H. Cichewicz, P. Crews, and T.R. Holman J. Med. Chem. 47 2004 4060
33. C. Fuganti, and S. Serra J. Chem. Soc., Perkin Trans. 1 2000 3758
34. T. Kimachi, and Y. Takemoto J. Org. Chem. 66 2001 2700
35. H. Hagiwara, T. Okabe, H. Ono, V.P. Kamat, T. Hoshi, T. Suzuki, and M. Ando J. Chem. Soc., Perkin Trans. 1 2002 895
36. M. Ono, Y. Ogura, K. Hatogai, and H. Akita Tetrahedron: Asymmetry 6 1995 1829
37. M. Ono, Y. Ogura, K. Hatogai, and H. Akita Chem. Pharm. Bull. 49 2001 1581
38. S.G. Burton Curr. Org. Chem. 7 2003 1317
39. S. Kobayashi, H. Uyama, and S. Kimura Chem. Rev. 101 2001 3793
40. A.M. Mayer, and R.C. Staples Phytochemistry 60 2002 551
41. N.C. Veitch Phytochemistry 65 2004 249
42. M. Antolovich, D.R. Bedgood Jr., A.G. Bishop, D. Jardine, P.D. Prenzler, and K. Robards J. Agric. Food Chem. 52 2004 962
43. S. Goldstein, D. Meyerstein, and G. Czapski Free Radical Biol. Med. 15 1993 435
44. V.C. Pham, A. Jossang, T. Sévenet, and B. Bodo Tetrahedron 58 2002 5709
45. J.A. Elix, V.K. Jayanthi, A.J. Jones, and C.J. Lennard Aust. J. Chem. 37 1984 1531
46. Y. Fukuyama, and Y. Asakawa J. Chem. Soc., Perkin Trans. 1 1991 2737
47. M. Jaspars, T. Rali, M. Laney, R.C. Schatzman, M.C. Diaz, F. Schmitz, E.O. Pordesimo, and P. Crews Tetrahedron 50 1994 7367
48. S. Miao, R.J. Andersen, and T.M. Allen J. Nat. Prod. 53 1990 1441
49. E.O. Pordesimo, and F.J. Schmitz J. Org. Chem. 55 1990 4704
50. K. Nomura, N. Suzuki, and S. Matsumoto Biochemistry 29 1990 4525
51. T.B. Freedman, X. Cao, R.K. Dukor, and L.A. Nafie Chirality 15 2003 743
52. T.B. Freedman, X. Cao, R.V. Oliveira, Q.B. Cass, and L.A. Nafie Chirality 15 2003 196
53. T.B. Freedman, X. Cao, L.A. Nafie, M. Kalbermatter, A. Linden, and A.J. Rippert Helv. Chim. Acta 86 2003 3141
54. L.A. Dailey, and P. Imming Curr. Med. Chem. 6 1999 389
55. Kenyon, V.; Chorny, I.; Holman, T.; Jacobson, M. J. Med. Chem., submitted.
56. L.A. Nafie Appl. Spectrosc. 54 2000 1634
57. C.R. Harrison, and P. Hodge J. Chem. Soc., Perkin Trans. 1 1982 509
58. H. Fulcrand, A. Cheminat, R. Brouillard, and V. Cheynier Phytochemistry 35 1994 499
59. C. Foppoli, R. Coccia, C. Blarzino, and M.A. Rosei Int. J. Biochem. Cell Biol. 32 2000 657
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.04, Gaussian, Pittsburgh PA, 2003.
61. T.R. Holman, J. Zhou, and E.I. Solomon J. Am. Chem. Soc. 120 1998 12564
62. A. Finazzi-Agro, L. Avigliano, G.A. Veldink, J.F.G. Vliegenthart, and J. Boldingh Biochim. Biophys. Acta 326 1973 462